Azanium;hydrate → HCID 66620714, compound

HRID 415217Notes

Reaction equation

HRID 415217 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:5]=[C:6]([C:10]2[O:11][C:12]3[C:18]([C:19]([O:21]C)=O)=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH:7]=[CH:8][CH:9]=1.O.[NH4+:24]>C(O)C>[CH3:1][NH:2][CH2:3][C:4]1[CH:5]=[C:6]([C:10]2[O:11][C:12]3[C:18]([C:19]([NH2:24])=[O:21])=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 22024077Azanium;hydrateHCID 66621015Methyl 2-(3-((methylamino)methyl)phenyl)benzo[d]oxazole-7-carboxylate

Product 1

HCID 66620714HCID 66620714, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

Methyl 2-(3-((methylamino)methyl)phenyl)benzo[d]oxazole-7-carboxylate (80 mg, 0.27 mmol) and ammonium water (75.7 mg, 2.16 mmol) were added to ethanol (30 mL) and the mixture was stirred at 30° C. for 1 hr. The resulting mixture was evaporated under reduced pressure and purified with Pre-HPLC to obtain 2-(3-((methylamino)methyl)phenyl)benzo[d]oxazole-7-carboxamide (16 mg, yield 21%). 1H-NMR (400 MHz, DMSO-d6) δ 2.62 (s, 3H), 4.29 (s, 2H), 7.48-7.52 (t, J=8 Hz, 1H), 7.70-7.74 (m, 1H), 7.81-7.83 (d, J=8 Hz, 1H), 7.90-7.98 (m, 3H), 8.34-8.43 (m, 2H), 9.06 (s, 2H); LC-MS (ESI) m/z 282 [M+1]+.

Workup

  1. customThe resulting mixture was evaporated under reduced pressure
  2. custompurified with Pre-HPLC

Sources & evidence

ORD record
ord-2efab43bc28e484fba1d997d7778645f
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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